Acid chromable monoazo dyestuffs and a process of making same



Patented Sept. 14, 1948 ACID CHROMABLE MONOAZO DYE STUFFS AND A PROCESS OF MAKING SAME Adolf Krebser, Riehen,

Basel, Switzerland, assignors to J. R. Geigy A. G., Basel, Switzerland, a Swiss firm No Drawing. Application March 10, 1945, Serial and Werner 1 Kuster,

In. Switzerland November 23,

Section 1, Public Law 690, August 8,- 1946 Patent expires November 23,1963

It has been found that valuable wool dyestuffs are obtained by diazotising amines of the general formula wherein X means a SO3I-I-group or a SOz-arylgroup and Y means a monoor polynuclear ohydroxy-carboXy-phenyl radical, and acid cou pling the same with amino-hydroxynaphthalene sulfonic acids of the general formula wherein R means hydrogen or an alkyl radical.

The new dyestufis dye wool from an acid bath in vivid red shades which, by an after-chromation, scarcely change their shades, but become substantially improved with regard to their fastness properties. The diazo components used for the production of these dyestuffs are obtained by condensing o-hydroXy-carboxy compounds of the benzene series containing amino groups, in presence of acid binding agents, with a 4- halogeno-3-nitrobenzoyl halide which may be further substituted, or by first substituting the 4- positioned halogen of the benzoic acid aryl compound, by means of sodium sulfite, by the sulfonic acid group or, by means of aryl sulfinic acid salts, by the aryl sulfone radical and finally reducing the same to the corresponding S-amino- 4 sulfobenzoic acid-o-hydroxy-carboxy-arylides or 3-aminol-arylsulfobenzoic acid. o hydroxycarboxy-arylides. As o-hydroxy-carboxy compounds of the benzene series may be understood for instance: 3- and 5-amino-Z-hydroxy-benzoic acids, 3-amino-5-methyl-2-hydroxybenzoic acid, 5-amino 3 methyl 2 hydroxybenzoic acid, 5- amino 4 methyl 2 hydroxybenzoic acid, 3- amino-5-sulfo-2-hydroxybenzoic acid, 5-amino- 3-sulfo 2 hydroxybenzoic acid, 4'-amino-3- methyl-4-hydroxy-diphenylmethane-5-carboxylic acid, 3"-amino-2:2'-dihydroxy-5:5'-dimethy1- triphenylmethane-3:3'-dicarboxylic acid and the like.

The present invention may now be illustrated, but not limited, by the following, wherein the parts are by weight, unless otherwise stated.

6 Claims. (01. zoo-#199 2 Errample 70.4 parts of 3-(3-amino-4'-sulfobenzoyl)- amino-Z-hydroxybenzoic acid are dissolved in neutral condition in 700 parts of water by means of sodium carbonate, intermixed with 200 parts of n-nitrite and, within half an hour, added to parts by volume of concentrated hydrochloric acid in 300 parts of water, the temperature being not allowed to rise above 5-7 C. Thus, the greatest part of the diazonium compound is precipitated. After complete diazotization a solution of 47.8 parts of Z-amino-S-hydroxynaphthalene-fi-sulfonicacid in 500 parts of water being slightly acid to litmus is added slowly to the obtained suspension. After completion of the dyestufi formation the whole is neutralised, heated to (3., treated with 10% of sodium chloride and, after-"cooling to 20 C., filtered. When dried, the dyestufi constitutes a red pow--: der which is easily soluble in warmwater and, which dyes wool from an acid bath in vivid red shades becoming somewhat more bluish on afterchroming.

Instead of 3- (3 -amino-4 -sulfobe-nzoyl) amino-z-hydroxybenzoic acid also other diazo components, such as 5-(3'-amino-4'-sulfobenzoyl)- amino-Z-hydroxybenzoic acid, 5-(3'-amino-4'- sulfobenzoyl) amino-3-methyl-2-hydroxybenzoic acid, 5-(6'-chloro-3-amino-4-sulfobenzoyl)- amino-Z-hydroxybenzoic acid, 4(3"-amino-4- sulfobenzoyl)-amino-3-methyl 4 hydroxydiphenyl-methane-5-carboxylic acid, 3"-(3"-amino-4'-su1fobenzoyl)-amino 2:2 dihydroxy- 5 5-dimethyltriphenylmethane-3 :3 -dicarboxylic acid, and the like maybe used.

What we claim is:

1. A process for the manufacture of an acid chromable monoazo dyestufi which comprises coupling in an acid solution 2-amino-8-hydroxynaphthalene-G-sulfonic acid of the formula with a diazoti sed amine of the formula 2 wherein Y stands for a radical of the benzene OH CODE 3. A process for the manufacture: or an acid" chromable monoazo dyestufi which comprises coupling in an acid solution 2-amino-8-hydroxya naphthalene-G-sulfonic acid with the .d'iazotised amine of the formula soon- 4. An acid: chromabl'e monoazo dyestuff of the fornmla s oiH. I IHQ z.- N=N- I SOsH whereinv Y stands; for a. radical' of the benzene series containing: at leastjaonev c-hydroxy-carboxy grouping, and Z; means: a member selected from the'g-roup consisting of H: and C1 being; abluish: red powder'and dyeing wool; in redishades remaining nearly unaltered when afterchromed'.

4 5. The acid chromable monoazo dyestuff of the formula SOaH NH2- being acarminer-red powder dissolving in water with" carmine-red color, in sulfuric acid with orange color and dyeing wool in red shades remaining nearly unaltered when afterchromed.

6'; The acid chromabl monoazo dyestuff of the being a carmine-red powder dissolving in water with carmine-red color, in sulfuric acid with redorange color and dyeing wool in red shades remaining nearly unaltered when afterchromed.

ADOLF KREBSER. WERNER KUSTER.

REFERENCES CITED- The following references are of record. in the;

file of this patent:

UNITED STATES PATENTS Number Name Date 2,232,870 Roos Feb. 25, 1941 FOREIGN PA'IENIS Number Country Date 457,840. France July 23, 191.3 648,769 Germany Aug. 7; 19137 

